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Bidentate Lewis Acid Catalyzed Inverse-Electron-Demand Diels-Alder Reaction for the Selective Functionalization of Aldehydes

Schweighauser, Luca and Bodoky, Ina and Kessler, Simon N. and Haeussinger, Daniel and Wegner, Hermann A.. (2012) Bidentate Lewis Acid Catalyzed Inverse-Electron-Demand Diels-Alder Reaction for the Selective Functionalization of Aldehydes. Synthesis, 44 (14). pp. 2195-2199.

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Official URL: http://edoc.unibas.ch/dok/A6083434

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Abstract

The inverse-electron-demand Diels-Alder (IEDDA) reaction catalyzed by a bidentate Lewis acid was applied to enamines generated in situ from aldehydes. In general, a high functional group tolerance has been observed. Side reactions during the enamine forming step can limit the yield of the desired naphthalene. For citronellal as substrate, the initial intermediate after the catalyzed IEDDA reaction was trapped by an intramolecular Diels-Alder reaction to furnish a tricyclic compound. This scaffold represents the framework of natural products such as valerianoids A-C or the patchouli alcohol.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Nuclear Magnetic Resonance (Häussinger)
UniBasel Contributors:Wegner, Hermann A. A. and Schweighauser, Luca and Kessler, Simon and Häussinger, Daniel
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:Georg Thieme
ISSN:0039-7881
Note:Publication type according to Uni Basel Research Database: Journal article
Identification Number:
Last Modified:29 Mar 2017 14:37
Deposited On:24 May 2013 09:04

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